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1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-r group phenyl) ethano and preparation method thereof

A dimethoxyphenyl and methoxyphenyl technology, which is applied in the preparation of carboxylate, nitrile, chemical instruments and methods, etc., can solve the problem of reducing cyclin protein expression, cell apoptosis, inability to complete, etc. question

Inactive Publication Date: 2005-10-26
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In 2001, Ahmad et al. [Ahmad N, Adhami VM, Afaq, et al. Resveratrol causes WAF-1 / p21-mediated G(I)-phase arrest of cell cycle and induction of apoptosis inhuaman epidermoid careinoma A431 cells. Clin Cancer Res, 2001 , 7(5):1466] reported that resveratrol can induce the cyclin-dependent protein kinase (CDK) inhibitory protein p21 WAF-1 , and can reduce the protein expression of cyclin D1, D2, E and CDK2, CDK4, CDK6, and then cause the G of human epidermal cancer A431 cells 1 phase pause so that the cell cannot complete the transition from G 1 Phase to S phase transformation, and this process is considered irreversible, will eventually lead to apoptosis
But as a cancer drug, resveratrol is not strong enough

Method used

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  • 1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-r group phenyl) ethano and preparation method thereof
  • 1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-r group phenyl) ethano and preparation method thereof
  • 1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-r group phenyl) ethano and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 1-carboxy-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene (3a)

[0034] 3, the preparation of 5-dimethoxyphenylacetonitrile (1):

[0035] Add 9.8 grams of sodium cyanide and 50 milliliters of water into a 250 milliliter three-necked flask, stir to dissolve the solid, add 50 milliliters of absolute ethanol, raise the temperature to 65°C, add 40 grams of 3,5-dimethoxybenzyl bromide, and The reaction was incubated for 1.5 hours. Pour out the reaction solution, cool to room temperature and precipitate a solid, filter to obtain a crude product, recrystallize from methanol / water to obtain 23 g of white needle-like crystals, melting point 51-53°C.

[0036] 3, the preparation of 5-dimethoxyphenylacetic acid (2):

[0037] In a 150 ml three-necked flask, 17.7 g of 3,5-dimethoxyphenylacetonitrile (1) and 50 ml of methanol were added, and the mixture was stirred and heated to dissolve the solid. Add 25 milliliters of water and 15 grams of sodium hydro...

Embodiment 2

[0040] Example 2: Preparation of 1-carboxy-1-(3,5-dimethoxyphenyl)-2-phenylethylene (3b)

[0041] Using a method similar to Example 1, 1.96 grams of 3,5-dimethoxyphenylacetic acid (2) was reacted with 1.1 grams of benzaldehyde to obtain white powder solid 1-carboxy-1-(3,5-dimethoxy Phenyl)-2-phenylethylene (3b) 1.7 g, melting point 203-205°C.

Embodiment 3

[0042] Example 3: Preparation of 1-carboxy-1-(3,5-dimethoxyphenyl)-2-(4-nitrophenyl)ethene (3c)

[0043] Using a method similar to Example 1, by reacting 1.96 grams of 3,5-dimethoxyphenylacetic acid (2) with 1.5 grams of 4-nitrobenzaldehyde, yellow needle-like crystals of 1-carboxy-1-(3,5 -2.2 g of -dimethoxyphenyl)-2-(4-nitrophenyl)ethylene (3c), melting point 226-228°C.

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Abstract

The present invention relates to a 1-carboxy-1-(3,5-dimethoxyphenyl)-2-(4-R group phenyl) ethylene and its preparation method, belonging to the field of organic chemistry and pharmaceutical chemistry. Said invention provides its general formula. Said preparation method uses 3,5-dimethoxy phenylacetic acid and correspondent para-orientating R group benzaldehyde and makes them produce reaction so as to obtain the invented product which can be used in the medicine field for resisting tumor and resisting oxidation.

Description

technical field [0001] 1-carboxy-1-(3,5-dimethoxyphenyl)-2-(4-Rylphenyl)ethylene and its preparation method relate to a class of 1,2-stilbene derivatives, belonging to fields of organic chemistry and medicinal chemistry. Background technique [0002] In 1989, the results of the epidemiological survey of the World Cardiovascular Disease Control System hosted by the World Health Organization (WHO) showed that the morbidity and mortality of coronary heart disease in the French were lower than those in other western countries, especially the Americans and the British. much. Although the French consume almost four times as much saturated fat as Americans and Britons, their risk of heart disease is only one-third that of the latter. This phenomenon is known as the "French Paradox". Studies have shown that this phenomenon is closely related to France being the world's largest wine producer and consumer. Analyzing the reason, it may be because there is a substance called resvera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/58
Inventor 罗世能朱玉松沈永嘉谢敏浩刘娅灵邹霈何拥军
Owner JIANGSU INST OF NUCLEAR MEDICINE
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